


They Took The Midnight Train Going Anywhere

by crossroadswrite



Category: Supernatural
Genre: Alternative Universe - 1920s, Blowjobs, Crodressing!Cas, Crossdressing, Explicit Sexual Content, Gangster!Dean, M/M, Prohibition Law, Speakeasies, Waiter!Chuck, dancer!cas, mafia
Language: English
Status: Completed
Published: 2014-04-30
Updated: 2014-04-30
Packaged: 2018-01-21 10:11:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,113
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1546970
Author URL: https://archiveofourown.org/users/crossroadswrite/pseuds/crossroadswrite
Summary: <blockquote class="userstuff">
              <p>“Who’s the hoofer?” he asks, pointing the tip of his cigar to the man moving in perfect sink with the music, some upbeat thing that makes the frilly ends of his dress bounce and shimmy.</p><p>“That’s Castiel, mister.”</p><p>Dean nods slowly, “Say Chuck, how many rubes do you want for me to have a chat with Castiel?”</p>
            </blockquote>





	They Took The Midnight Train Going Anywhere

**Author's Note:**

> Another of my 1K GIVEAWAY fics, for the lovely blushingmisha on tumblr.
> 
> This fic has quite a lot of 20s slang, but never worry, you just have to hover over the slang-y words to know what it means.
> 
> Everyone knows where this title came from, I neednd't say anything.

_I’m proud of you, son._

Those are the exact words John Winchester told his son the first time he killed a man. Dean had been barely seventeen in his way too big suit and with shaking and sweaty hands. The guy had been twice his size, a burly thing that made the very grave mistake of disclosing the location of one of their safe houses to a rival family.

He remembers the pat on the shoulder his father had delivered along with those praising words. It had been the kindest he’d been to Dean since his mom died, the proudest he’d been of him. From then on killing and doing the family business had been synonym of love.

Dean had always been good with following the rules, being the perfect little soldier for his dad. Of course that as of late, he had been straying a little bit from the careful tracks his dad set for his life. With Sammy gone and his dad’s mood being more often sour than not, he’d start needing a little something to keep himself going every day.

Protecting the family wasn’t as easy without any actual family worth protecting. He had a job though, a duty of keeping the family business alive and going.

Even if he’d sneak into speakeasies to have a couple of drinks, meaning heavy liquor, and cigars with a bunch of man who knew the hails of the prohibition law, what it was like to go through life without that extra kick that pushes you forward.

Tonight has been a particularly bad night for Dean. They’d lost one of their own to the cops and another one to a rival family that thought it smart to kidnap and ask for ransom.

Ah! That’s turned out well for them. Let’s just say that their lineage ended there.

On top of that, his father had yelled at him a bit for letting the situation get to that point and made him torture some John for info.

If there was something Dean actively hated it was torturing. There was just something wrong and cowardly about having someone defenseless at their mercy and taking advantage.

Obviously the thing to do was find the closest speakeasy and drown his sorrows in liquor and pretty girls in flashy dresses.

There was this place highly recommended by Michael, the respected (hot as hell) leader of the Angeles family, who kept friendly business with the Winchesters.

 _Little Slice of Heaven_ , the place was called, fronting as a bakery with a speakeasy in the basement.

Dean rasped on the door, and a slim guy poked his head out, looking him over once before throwing the door back and letting him in.

Dean Winchester was well known around these parts, it would be almost an insult if the guy had asked who he was or denied him entry. A finger loosing insult at that. Anyone who stood too close between Dean and his liquor wasn’t in a very safe place to begin with.

This club _was not_ what Dean had anticipated though. There were drinks and cigars in abundance alright, but the people in the pretty dresses up on the stage and swaying around the patrons were very decidedly not girls.

And oh, wasn’t that just grand! A place where Dean could drown his sorrows and pursue his interest in well-built men who could give him a good time, past time he couldn’t really afford to practice on a daily basis since _God_ forbade such behavior between two men. Good thing Dean didn’t believe much in God then.

He sits himself in the corner, with a good enough view of the stage and the bar. The smoke of cigars is heavy in the air, the hushed talk of men dotted with raucous laughter fills the air as something jazzy and smooth plays on the background, the dancers up on the stage with their shiny dresses swaying to it effortlessly.

Dean knows how these kinda juice joints work. The more influence you have on the outside the better quality it is the liquor they serve you.

He flags the barkeep and the man rushes over, taking his order and giving him a cigar _on the house, Mr. Winchester_.

Soon, he has everything he needs to recuperate his night. Lift his spirits up a little bit, and that’s when he notices him, rising to the stage, the spotlight following him and his shimmering blue dress.

He’s damn gorgeous, messy dark hair that gives the feel someone just tugged at it for hours on head, plump and chapped lips that are just perfect for kissing and the most penetrating blue eyes, which, for a single moment, catch Dean’s in the crowd and hold them for a little while, a smirk appearing on the dancer’s face and that’s it.

Dean flags the waiter, a nervous looking guy with a sad attempt of a beard and shifty eyes, _call me Chuck, please_.

Chuck leans close, wrinkling his nose, when Dean blows smoke into his face distractedly.

“Who’s the hoofer?” he asks, pointing the tip of his cigar to the man moving in perfect sink with the music, some upbeat thing that makes the frilly ends of his dress bounce and shimmy.

“That’s Castiel, mister.”

Dean nods slowly, “Say Chuck, how many rubes do you want for me to have a _chat_ with Castiel?” he asks, rolling the foreign name in his mouth, trying it on for use and finding out it fits perfectly on his tongue.

Chuck seems startled by the question, “I- I don’t-“

Dean rolls his eyes and smiles down at him, “How much? Just for a _chat_ , me ‘n’ him.”

Chuck rolls his shoulders uneasily but ends up muttering a price, watching with greedy eyes as Dean takes a wad of cash out of his inner pocket and unclips a few tens, passing it over to the tiny man.

As soon as the song playing ends, Chuck leads Castiel to his table, the dancer following him with light steps, lips pinched.

“This is the mister who wanted to _chat_.”

Castiel seems startled, giving him the once over, and smirking when he likes what he sees. He sits himself down in front of Dean, hands on his lap and a cautious look on his face, even if he does like what he sees you can never be too careful with gangsters.

“Castiel Collins,” he introduces himself.

Dean nods and smiles, extending his hand for him to shake, because if there’s something his momma taught him while she was still alive it was manners, “Dean Winchester.”

The man in front of him nods like this isn’t new information, “I know who you are.”

Dean smirks and nods his head, acknowledging him. There are little people in this town that _don’t_ know who he is after all.

“Has anyone ever said you’re a sheik?”

Castiel blushes a pretty shade of red, “You’re just sayin’ a line.”

Dean shakes his head and smiles, “You have it. Pretty little doll like you should hear it every day. You have the smarts to know it too.”

He takes a careful sip of his drink, gauging Castiel’s reaction carefully, “Do I now?”

The man seems amused, “You do,” he confirms easily.

“What do you want?”

“Take you for a ride. Show you a real good time. Even if the bank’s closed.”

Castiel eyes him carefully, “You sure that ain’t just the giggle water talkin’?”

Dean shakes his head once, taking a long drag of his cigar and carefully blowing smoke rings. So yeah, he’s trying to impress a little bit, so sue him.

“You’re gorgeous, baby.”

Castiel’s pretty little blush darkens and the other man slowly gets up from his seat, turning to go away and well ain’t that such a shame. Dean slumps against his seat in defeat.

If the dancer isn’t interested, he won’t force himself on him. He wasn’t raised like that.

“You comin’, bimbo?” Castiel throws over his shoulder, dropping his eyelids and giving Dean a coy smile.

It is almost hilarious the speed with which Dean scrambles out of his seat, putting his cigar out and catching up to the pretty dancer.

Castiel- Cas, Dean decides to call him- grabs a hold of his hand and tugs him toward the back, to a little wooden door, almost hidden in the narrow hallway beside the touch.

He tugs Dean inside with a smile, locking the door behind him and slowly backing the gangster against it, until their mouths are mere inches apart.

“cash or check?” he inquires cheekily.

Dean doesn’t even dignify that with an answer, pulling Castiel to him and melding their lips together.

Castiel is forceful, rough hands bunching in the fabric of Dean’s shirt, pulling and tugging and gripping, forcing Dean’s mouth open and _no,_ that’s not what he needs right now. He needs slow and sweet and careful. He’s had enough violence for one day as it is.

He slows him down, gentle hands gripping Cas by the neck, his thumb under his jaw so he can angle Cas’s head just right, kissing him nice and slow, tongue lazily exploring Cas’ mouth, ripping a moan from the other man.

Cas’ hands grip at his sides, bunching his shirt in his fists and pulling Dean closer to him, finally getting along with a plan.

Dean slowly slides his hand down Cas’ torso, squeezing his hip once, before trailing his hands to Cas’ ass and giving him a squeeze, pushing Cas’ hips towards his own.

“Gorgeous,” he mumbles against the dancer’s lips distractedly, slowly walking him backwards to his the sofa, laying Cas down on it gently before he climbs between the man’s hips, both hands splayed on his thighs, pushing his dress up and reaching for the other man’s mouth, picking him up where he’d left off.

Castiel, delicious, responsive Castiel, slips his hands under Dean’s shirt, fingers tracing his ribs, the muscles in his back, racking his short nails on Dean’s back, before he settles those careful hands on Dean’s bottom, kneading his fingers in and dragging him down so their hips slot together in delicious friction.

Dean kisses his jaw, nips at it making his way down his neck with soft little pecks that have Cas throwing his head back, exposing the smooth expanse of his throat for Dean to do as he pleases with it.

Slowly, Dean drags Cas’s dress all the way up past his waist, thumbs hooking on his undergarments and pulling them down, down, down and slipping them free.

“Gonna treat you right,” he whispers, scooting backwards a bit so he can sit between Cas’ legs.

Castiel looks absolutely gorgeous like this. Flushed cheeks, hands clutching the sofa and lips slightly parted, panting.

He wants to put that look on his face again.

But for now he’ll just have to show Castiel a real nice time, so he lowers himself carefully, eyes trained on Cas as he pops his mouth open and takes him in his mouth, revealing in the slight hitch of Cas’ breath when he closes his mouth around the head of his cock and sucks, hollowing his cheeks.

Cas moans underneath him, one hand twining in Dean’s head as he moves slowly down, taking more and more of Cas’ length in his mouth.

Dean bobs his head up and down, swirling his tongue over the head of Cas’ cock, he takes his time, going nice and slow, making Cas crazy with it, making Cas moan and gasp so prettily for him.

Castiel tugs on his hair lightly, pulling him off and thrusting a can of Crisco to him, and Dean doesn’t really know where he got it or why he had that at hand in the first place, but he’s not about to dwell on it too much, popping it open and coating two fingers with it, to open Castiel up for him.

The dancer widens his legs, and cants his hips up, giving Dean plenty of room to work it.

Dean kisses his thigh once, before slowly, thrusting one finger into his tight hole, working it in and out slowly, crooking it, until he can add another one and start to scissor Castiel open, all the while given little kitten licks to head of Cas’ cockhead to get him to relax.

He crooks his fingers just right and Cas cries out, thrusting his hips up blindly, trying to get some friction and damn he’ll hurt himself if he bows his back off the couch like that again.

Dean tries to help him settle down, holding him down with his free hand and running his thumb soothingly over Cas’ beautiful hipbones.

He manages to add a third finger, before Cas starts thrusting down on his fingers and babbling nonsense, reaching for Dean’s hand and saying he’s ready “Please, please. Need it.”

Dean’s more than happy to comply, pulling his fingers back and reaching for his belt buckle, only to have his hands bat away by Cas, who takes the job into his hands.

“Switch,” he mutters, trying to get Dean under him, and that’s okay to. Dean goes willingly, lifting his hips when Cas starts to pull his pants down to free his leaking cock.

Castiel rubs Crisco into his palms, stroking Dean slowly, coating him with it, making dirty moans spill from his lips.

When he’s happy with his work, Castiel grips the base of Dean’s cock and lowers himself on it, taking a moment to adjust himself.

Dean traces his neck with one finger lightly, gripping the back of it and smoothing his thumb over Cas’ clean shaved jaw.

Cas drops his mouth open, his baby blues staring right into Dean, pupils blown and looking oddly fond.

He twists his head and kisses Dean’s thumb, splaying his hands in Dean’s chest to get good leverage. Carefully Castiel lifts himself up and slams back down, mouth dropping open on a gasp, echoed by Dean at the wonderful sensation surrounding him.

He grips Cas’ waist with one hand, helping him lift up and slamming back down again, start a rhythm that works perfectly for both of them.

Castiel is gorgeous above him, eyes closed and head thrown back, chasing his high. He’s beautiful like this and Dean can’t really stand standing so far away from him.

He sits up effortlessly, one arm going around Cas’ hips bringing him up and slamming him down in the most delicious of ways, bringing his mouth against Castiel’s, kissing him as good as he knows.

Something about the new angle must really work for Cass because he gets desperate, quickening his pace, undulating his hips in the most delicious of ways, whimpers and moans and broken pleas escaping his pretty chapped lips, the frilly ends of his blue dress bouncing happily against his thighs, in time with Cas’ thrusts.

Dean’s so close he can almost taste it, but he wants Castiel to come first, he wants to be _good_ for him, so he clenches his teeth and pistons his hips up once, twice and Cas falls apart around him clenching around Dean and coming all over that pretty dress of his. And that’s about all that Dean can take, before he bites down on Cas’ shoulder and comes in hot spurts inside the blue eyed man, his mind going blissfully blank for a few seconds.

He comes down from his high slowly, with Cas draped over his chest, panting and smiling and satisfied, proof that Dean can be good, that he doesn’t break everything he touches.

“I wanna keep you,” he mumbles, kissing Cas’ neck slowly, little pecks here and there that have the other man shivering, before he pulls away from Dean and lifts himself off of him, grabbing his underwear from the floor and slipping them back on.

He smiles kindly at him, almost sadly “What’d we do then? I’d be your moll and you’d be my daddy? None of those God fearing folk would approve. I doubt the big cheese would too.”

Dean clenches his teeth and tucks himself back in his pants, buckling his belt and rising to his feet.

“We could run,” he says, a beautiful idea taking home in his brain. Because yes they could ran away, just like Sammy had done. He could turn his back and never hurt anyone again.

“What for? To be bumped off by your family?”

“Catch the next train outta the station,” he continues, pleadingly, grabbing for Cas’ hand

“That’s baloney! They’d catch up to us.”

“I’d buy you a handcuff, even if it wasn’t official. I would.”

That brings Castiel short. Dean’s pretty sure he stops breathing for a while, “Yo-you would?”

He jerks his head up and down, twining their fingers together, “I’d give you the moon if you asked.”

Cas looks down, brows furrowed. When he looks back up to Dean he’s smiling “Okay.”

Dean grins and sweeps him into his arms, kissing him.

Dean waits for Cas to change into acceptable clothes and pack a small suitcase with everything he wants to take with them, before they stop by a bus station lockers where Dean already has a suit with everything he’ll need and enough money for them to make a living of for three months at least. It’s just a precaution measure in case the cops ever come after him.

They arrive at the train station at four a.m. and buy a ticket for the first train leaving this godforsaken town, careless about their destination.

In insight, Dean should really have expected for his father to catch up to him. Owning half the town should have given him the heads up that maybe he should’ve more careful, more discreet, but hell he’d been too wrapped up in Cas’ smile and Cas’ to care for any of that.

“Dean!” his father’s booming voice echoes through the train station, flanked by Christian and Gordon and of course he’d choose the two men that hate Dean’s gut, of course “What are you doing, boy? Leave that whore and get back here.”

The trainman hollers that the train is about to leave.

Dean ignores his father, turning his back on him and helping Cas up unto the train, passing him their bags.

“Step foot on that train and you’ll stop being family,” his father threatens.

The trainmen hollers one more, the train starting up.

Dean steps on the train, wrapping one arm around Cas’ waist and pulling him further into the train.

Castiel is eyeing him carefully, but he only smiles wide and asks, “Where are we going?”

His dancer smiles right back at him, “Anywhere.”


End file.
